HU230838B1 - Selective herbicidal compositions containing heteroaryloxy-acetamide derivatives - Google Patents

Description

Selective herbicidal compositions containing a heteroanloxyacetamide derivative

The present invention relates to a novel synergistic active compound combination having a selective herbicidal action, which comprises both known heteroaryloxyacetamide derivatives and known herbicidal compounds and / or compounds for improving the efficacy of crop plants, and which is particularly useful in selective cultivated plants.

The heteroaryloxyacetamide derivatives are potent and especially potent herbicidal agents against monocotyledonous weeds, which are the subject of several patents (e.g., EP 5501, EP 18497, EP 29171, EP 94514, EP 100044, EP 100045, EP 161602, EP 195237). EP 348737 and DE 4317323). However, the efficacy and / or crop specificity of such compounds is not always satisfactory.

Also known are synergistic active compound combinations of hepheraaryloxyacephamide derivatives and other herbicidal compounds (e.g., WO 94/02014, WO 96/07323, WO 98/11575, WO 98/17519, WO 98/08383, US 5858920, US 5,945,379 and U.S. Pat. 5985797) and heteroaryloxyacetamide derivatives! and herbiclds are active compound combinations of chemicals that enhance the ability of a crop to be cultivated (e.g., DE 3418167 and US 5858920). However, the application properties of such combined products are not always fully satisfactory.

Surprisingly, it has been found that certain known active substances of the heteroaryloxyacetamide derivatives, when used in combination with known herbicidal compounds of different classes and / or crop plants for improving their seed germination, have a distinct synergistic effect on controlling weeds and / or significantly particularly useful as a broad-spectrum combination preparation for selective weed control in crop crops such as cotton, barley, maize, potato, rape, rice, soy, sunflower, wheat and sugar beet.

The present invention therefore provides a selective herbicidal composition comprising an effective amount of a combination of active ingredients comprising the following components:

i 17634-1? BP SL

Compound (a), which is N-isopropyl-N- (4-fluorophenN) -α- (5-trifluoromethane-1 _→ 3,4-thiadiazole-2-yl) -XXi} -acetamide (Flufenacet) ("Drug Group 1") and (b) a compound which is 2-chloro-3- [2-chloro-5- (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-4-methyl) -2- ethyl) phenyl-2-propanoic acid ethyl ester (cinidone ethyl) ("2 active ingredient groups") and optionally (c) a crop tolerant compound of the following group: 4-dichloroethyl-1-oxa-4-aza-sp. ro [4,5] -decane (AD-67), 1-dichloroacetylhexahydro-3,3,8a-methylpyrrolo [1,2-a] pyrimidin-8 (2H) -one (dicyclone, BAS-145138) , 4-Dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benzoxacor), 5-chloroquinoline-8-oxy-acetic acid (1-methylhexyl ester) (cloquintocet-mexyl), α- (cyanomethoximino) -phenylacetonitrile (ciomethrin), 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) ethyl) -N- (2-propenyl) - Acetamide (DKA-24), 2 _L 2-Dichloro-N _< N-dl-2-propenylacetamide (dichlormid), N- (4-Methylphenyl) ~ N '~ - (1-Methyl-1-Phenyl) ethyl) urea (dimron), 4,8-dichloro-2-phenyl-pyrimidine (pentachlorim), 1- (2,4-dichlorophenyl) -5-trichloromethyl-1H-1,2,4-triazolyl; 3-Carboxylic acid ethyl ester (Fenchlorazole ethyl), 2-chloro-4-trifluoromethylthiazole-5-carboxylic acid phenyl methyl ester (flurazole), 4-chloro-N- (1,3-dioxoxan-2-ylmethoxy) - "trifluoro-acetofenonoxim (fluxofenim), 3-dikíóracetil ~ 5- (2-furaníS) -2,2-dimethyl-oxazolidine (furilazcl MON-139ÖO) et.íl-4,5-dihydro-5 _i-5 diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), diethyl-1 - _(2-i 4 díklórfenli) _-4! 5-Dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (Nephenpyr diethyl), 2-dichloromethyl-2-methyl-1 _: 3-dioxoxane (MG-191), 1,8-naphthalic anhydride o .- _(1, 3-dioxolan-2-yl-methoximino) -phenylacetonitrile (oxabetrinil), 2,2-dichloro-N- (1,3 ~ dioxol-2-ylmethyl) ~ N- (2 -propenyl} -acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyloxazolidine (R-28725), S-dichloroacetyl-4,6-methylmethyloxazolidine (R-29148), 1- (2-chlorophenyl) ) -5-phenyl-1H-pyrazole-3-carboxylic acid methyl ester and N- (2-methoxybenzoyl) -4 ~ - [(methylaminocarbonyl) amino] benzenesulfonamide ("active substance group 3"),

The active ingredient of Group 1 is known from the above-described patents,

Based on the chemical structure of the compound of the 2 active substances, it is classified into the following classes:

arylheterocyclic compounds (e.g., azafenidine, benzfendizone, butafenacylallyl, cinidone-ethyl, oxaziclomefon, proflurazole)

In particular, the composition according to the invention comprises a Group 1 active ingredient, a Group 2 active ingredient and optionally a Group 3 active ingredient.

Surprisingly, it has been found that the above defined active compound combination of a heteroaryloxyacetamide derivative and the specified Group 2 active ingredient exhibits particularly high herbicidal efficacy, particularly in barley, potato, maize, rice and in various crops, , in soya and wheat cultures, can be used for selective weed control against monocotyledonous and dicotyledonous weeds, which can also be used for monocotyledonous and dicotyledonous weeds in the semi- and non-selective range.

Surprisingly, the herbicidal efficacy of the active compound combination according to the invention is significantly higher than the sum of the activity of the individual active substances.

Therefore, the active compound combination according to the invention exhibits an unforeseen synergistic effect and is not a simple supplement. The new drug combination is well tolerated in many cultures and can also be used against otherwise difficult to control weeds. The new active compound combination therefore represents a valuable enrichment of herbicides.

The synergistic effect of the active compound combination of the invention is particularly pronounced at defined concentration ratios. However, the weight ratio of the active compounds used in the active compound combination can be varied within a relatively wide range. Generally 0.01 to 1000 parts by weight, preferably 0.02 to 500 parts by weight, particularly preferably 0.05 to 100 parts by weight, of active ingredient 2 are used per 1 part by weight of the active ingredient in Group 1,

The following compounds are particularly preferred as a combination partner for Group 3 of the active compounds: 5-chloroquinoline-8-oxoacetic acid (1-methylhexyl ester) (cloquintocetmexyl), ethyl 4,5-dihydro-5,5-diphenyl · 3-isoxazolecarboxylate (isoxadiphenethyl) and diethyl 1- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr diethyl) a. improving the bearing capacity of cereals, and

4-dichloroacetyl-1-oxa-4-aza-spiro [4.5] decane (AD-67), 1-dichloroacetylhexahydro-3,3,8a-trimethylpyrrolo-1,2-a] pyrimidine-6 ( 2H) -one (BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (henoxacor), 2,2-dichloro-N, N-di-2 ~ propenyl-acephamide (dichloride), 2,2-dichloro-N- (2-oxo-2- (2-propenylamino) ethyl) -N- (2-propenyl) acetamide (DKA-24), 3-dichloroacetyl; -5- (2-furanyl) -2,2-dimethyloxazolidine (furilazole, MN-13900). 3-Dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148) for improving the removability of maize.

Exemplary active compound combinations of the invention, optionally containing safener, include the following combinations: flufenacet + cinidone ethyl

It is surprising that, among the large number of known safeners or antidotes that antagonize the herbicide's effects on the crop, the compounds given in Group 3 are suitable compounds of Group 1 and their salts, and combinations thereof with Group 2. has to do with the harmful effects on crops! without affecting herbicidal efficacy on weeds.

According to the invention of active ingredients of group 3 elviseihetőségének for enhancing crop plants may also be used without the use of active ingredients of group 2 active compound of Group 1, the following compounds: 1-diklöracet l-hexahydro-3 _I 3 _t ~ 8a tnmetilpírrolo ( 1,2-ay-Pinnimidin-6 (2H) -one (dicyclone, BAS-145138), ethyl-4,5-dihydro-5,5-diphenyl-3-isoxazoicarboxylate (isoxadiphenethyl), diethyl-1- (2) , 4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr diethyl), 3-dichloroethyl-2,2-dimethyl-oxazolidine (R-28725), 3-Dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148) and 1- (2-Chloro-phenyl) -5-phenyl-1H-pyrazole-3-carboxylic acid methyl ester .

The beneficial effect on the crop tolerance of the active compound combination according to the invention is also particularly pronounced at certain concentration ratios. However, the weight ratio of the active compounds used in the active compound combination can be varied within a relatively wide range of 1 part by weight to the active ingredient of Group 1 or its active ingredients. One or more of the active ingredients in Group 3 are generally used in an amount of from 8.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, particularly preferably 0.1 to 10 parts by weight, based on the mixture thereof.

Any plant or plant part can be treated within the meaning of the invention. By plant is meant any plant or plant population, such as a desired or undesired wild plant or crop (including naturally occurring crop plants). The crop is some standard breeding! or a plant produced by optimization processes, or a plant produced by biotechnological and genetic engineering methods or combinations thereof, including transgenic plants and plant varieties which may or may not be protected. The plant part can be any part or organ of the plant above or below ground, such as shoots, leaves, flowers and roots, camels, needles, stems, branches, flowers, fruits, seeds, roots, tubers and rhizomes. Plant parts include fruit and vegetative and generative propagation material such as shoots, tubers, rhizomes, cuttings and seeds,

The active compound combination according to the invention can be applied directly to the plants or parts of plants or to their environment, habitat or storage space by conventional methods of treatment, such as dipping, spraying, spraying, spraying, spreading or propagating, especially single or multilayer coating.

Examples of plants produced by biotechnological and genetic engineering methods or combinations of such methods include so-called 4-HPPD, EPSP and / or PPO inhibitory plants such as acuron plants.

For example, the following plants can be advantageously treated with the active compound combination according to the invention:

Dicotyledonous weeds: Abutylon. Amaranthus, Ambosia, Anoda, Anthemis, Aphanes, Atríptex, Bellis, Bídens, Capselía, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convoivulus, Datura, Desmodium, Emex, Erysímum, Euphorbia, Galeopsis, Gainsoga Kocbía, Lamium, Lepidium, Undernía, Matricaria, Mentha, Mercuriahs, Mullugo, Myosotis, Papaver, Pbarbitis, Plantago, Polygonum, Portulaca, Ranuncuius, Rapharius, Rorippa, Rotia, Rumex, Sansoia, Senecio, Sesbanía, Sesbanía Sonchus, Spbenociea, Stearia, Taraxacum, Thlaspí, Tripoli, Llrtíca, Veronica, Vioía, Xanthium,

Dicot cultures: Aracbis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glyoine, Gossypium, Ipomoea, Laotuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Písum, Solanum, Viola.

Monocotyledonous weeds: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyioctenium, Digitaria, Echinocbioa, Eieocharis, Eeususa, Eragrostis, Eragrostis, Eragrostis , Leptochloa, Loiium, Monochoria, Panicum, Paspalum, Phalaris, Phíeum, Poa, Rottboeilía, Sagittaria, Scirpus, Setaria, Sorghum.

Monocot cultures: Ailium, Ananas, Asparatus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticate, Triticum, Zea.

However, the utility of the active compound combination according to the invention is not limited to the plants listed herein, but extends to other plants in the same way.

The active compound combination according to the invention can be used in conventional crops (such as row crops planted at appropriate row spacing), in plantations (such as grapes, fruits and lemons), and in industrial areas, tracks, tracks. and fields, as well as stubble management and minimally cultivated areas. It can also be used for burning (weed control, for example in potato culture) or as a defoliant (for example, in cotton culture). It can also be used in fallow land, as well as in nurseries, forestry and ornamental plants.

The active compound combination can be formulated into standard formulations, for example, oat, emulsion, spray powder, suspension, powder, dusting agent, paste, soluble powder, granulate, suspension-emulsion concentrate, natural or synthetic material impregnated with an active ingredient, and incorporated into a polymeric material.

These formulations are prepared in a known manner, for example, by incorporating the active compounds with excipients, i.e., liquid solvents. and / or in admixture with solid carriers, which may optionally include surfactants, i.e. emulsifiers and / or dispersants and / or foaming agents.

If water is used as a carrier, an organic adjuvant may also be added. Suitable liquid solvents are, for example, an aromatic compound such as xylene, toluene or alkylS-naphthalene; chlorinated aliphatic or aromatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride; an aliphatic hydrocarbon such as cyclohexane or paraffin such as petroleum fraction; mineral or vegetable oils; alcohol, so butane! or glyco, and their ethers and esters; a ketone such as acetone, methyl ethyl ketone, methyl isobufyl ketone or cyclohexanone; a highly polar solvent such as dimethylformamide, dimethylsulfoxide and water.

Solid carriers include ammonium salts, natural stone flour such as kaolin, clay earth, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic stone flours such as high-fumed silica, alumina and silicates. In the case of granules, natural rocks such as crushed stone, marble, pumice stone, sepiolite, doomite as well as synthetic particles derived from inorganic or organic flours and organic materials such as sawdust, coconut shells and corncobs may be used as solid carriers.

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non-ionic and anionic emulsifiers, such as poly (oxyethylene) fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. sulfonates and egg protein hydrolyzate; as dispersants, for example, lignin-sulphite impurities and methylcellulose.

The formulations may also contain binders that promote adhesion, such as carboxymethyl cellulose. natural and synthetic polymers in powder, granular or latex form, such as gum arabic, poly (vinyl acetate), poly (vinyl acetate), and natural phospholipids, such as cephalins, lecithins and synthetic synthetic phospholipids, and mineral or vegetable oils.

Dyes such as inorganic pigments such as iron oxide, titanium oxide, ferrocyanite and organic dyes such as alizarin, azo, metal phthalocyanone and trace elements such as iron, manganese, leather, copper, cobalt, molybdenum and zinc salts may also be used. too.

The compositions generally contain from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight, of the active ingredient.

The active compound combination of the present invention is generally employed in the form of a finished formulation. However, the active ingredients in the active compound combination may be formulated for use in individual formulations, for example in tank mix.

The new active compound combinations may be used alone or in admixture with other known herbicides in ready-to-use formulations or in tank mixes. . For certain uses, particularly post-emergence applications, it is also advantageous to admix the mineral or vegetative oil (e.g., "Oleo DuPont 11 E ^!! ") or an ammonium salt, such as ammonium sulfate or ammonium rhodanide, as an additive for plants.

The active compound combination of the present invention may also be used in the form of a commercially available formulation or a ready-to-use formulation thereof. Examples include ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. The application is carried out in the usual manner, for example by irrigation, spraying, dusting or spraying.

The active compound combination according to the invention can be applied by incorporation into the soil before and after emergence of plants and before planting.

For herbicides, there is a synergistic effect when the herbicidal efficacy of the active compound combination is greater than that of the active ingredients used alone.

For a given combination of two herbicidal agents, the expected effect can be calculated by the following equation (COLBY, S.R., "Calculating synergistic and antagonistic response of herbicide combinations", Weeds, 15, 20-22 (1967)):

E ~ X + Y- (X «Y / 10G) where

X is the percentage effectiveness of herbicide A (Group 1 active ingredient) at p kg / ha application rate,

Y is the percentage effectiveness of herbicide B (Group 2 active ingredient) at q kg / ha application rate,

E is the expected efficacy of herbicide A and B at p + q kg / ha application rate.

If the measured efficacy is greater than the calculated efficacy, the efficacy of the combination is greater than the additive effect, i.e., a synergistic effect.

In fact, the active compound combination according to the invention has such properties! provides that the measured herbicidal activity is stronger than the calculated effect, that is, the new active compound combination exhibits a synergistic effect.

Claims (7)

Claims What is claimed is: 1. A composition comprising an effective amount of an active compound combination, wherein the combination comprises the compound (a) which is N-isopropyl-N- (4-fluorophenyl) -α- (6-trifluoromethyl-1,3,4-thiadiazole). 2-yloxy) acetamide (flufenacet) (., the first active group ") and (b) compound which is 2-chloro-3- [2-chloro-5- (1,3,4 _i 5 _t 6 , 7-Hexahydro-1,3-dioxo-2H-isoindol-2-yl) phenyl] -2-propanoic acid ethyl ester (cinidone ethyl), ("active ingredient group 2") and optionally (c) crop tolerant compound from the group: 4-dichloro-1H-1-oxa-4-aza-spiro-4,453-decane (AD-67), 1-dichloroacetylhexahydro-3,3 _, 8a-trimethylpyrrolo (1,2- a] -pyrimidin-6 (2H) -one (dicyclone, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benzoxacor), 5-chloro-choline choline. 8-Oxyacetic acid (1-methylhexyl ester) (cloquintocet-mexyl), α- (cyanomethoxyimino) phenylacetonitrile (ciometrinyl), 2,2-dichloro-N- (2-oxo-2- (2-propene) lamnino) ethyl) -N- (2-propenyl) acetamide (DKA-24), 2,2-dichloro N, N-di-2-propenylacetamide (dichlormid), N- (4-methylphenyl) - N '- (1-Methyl-1-phenylethyl) urea (dimethron), 4,6-dichloro-2-phenylpyrrolidine (feniorim), 1- (2,4-dichlorophenyl) -5-trichloromethyl-1 H -1-trans-Thiazole-5-carboxylic acid ethyl ester (Fenchlorazol-ethyl), 2-chloro-4-fluoromethyl-thiazole-8-carboxylic acid phenylmethyl (fururazole), 4-chloro-N- (1,3- dioxolan-2-ylmethoxyb-o-trifluoroacetophenone oxime (phixofenim), 3-dichloroacetyl-5- (2-furanyl)-2,2-dimethyl-oxazolidine (furilazole, MON-13900), ettl-4,5- dihydro-5,5-diphenyl-3-isoxazole-carboxylate (isoxadiphenethyl), diethyl-1- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1H-pyrazole-3,5- d-carboxylate (mefenpyr-diethyl), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-Ί 91), 1,8-naphthalic anhydride, - - (1,3-dioxoxanane). 2-yl-methoximino) -phenylacetonitrile (oxabetrinyl), 2,2-dichloro-N- (1,3-dioxo-2-yl-methyl) -N- (2-propenyl) -acetamide (PPG-1292 ), 3-Chloroacetyl-2,2-Dimethyl-oxazolidine (R-28725), S-dichloroacetyl-η 5 -methyloxazolidine (R-29148), 1- (2-chlorophenyl) -5-phenyl-1 H -pyrazole-3-carboxylic acid methyl ester and N- ( 2 Methoxybenzoyl) -4 - ((methylaminocarbonyl) amino) benzenesulfonamide ("3. drug group) A composition according to claim 1, which comprises as active compound (c) a crop plant enhancer (c). 5-Chloro-quinoline-8-oxo-acetic acid (1-mephylhexyl ester) (cloquinol ethoxymethyl) and dimethyl-1- (2,4-dichlorophenyl) -4,5-dihydro-5-methyl-1 H -pyrazol-3 , 5-dicarboxylate (mefenpyr diethyl). 3, 1-2. A composition according to any one of claims 1 to 6, containing from 0.91 to 1000 parts by weight of compound (b) from active ingredient group 2 of the berbicides, based on 1 part by weight of compound (a) of the active ingredient group. 4. A composition according to any one of claims 1 to 5, containing from 0.001 to 1000 parts by weight of one or more of the active ingredients of the crop group (1) per crop component of compound 1 (a) or a mixture of herbicides derived from active ingredient 2 (b). o) the component. 5. Use of a composition according to any one of claims 1 to 3 for controlling unwanted plants. 6. A method for controlling unwanted plants, characterized in that the unwanted plants and / or their habitat 1-4. A composition according to any one of claims 1 to 6. 7, A process for the preparation of a herbicidal composition, characterized in that a method according to any one of claims 1-4. A composition according to any one of claims 1 to 6, mixed with a surfactant and / or carrier.